


Trial and Error (Kink Series Part 1 )

by sinfuldesire_archivist



Category: Supernatural
Genre: Angst, During Canon, Established Relationship, Kinks
Language: English
Status: Completed
Published: 2011-06-01
Updated: 2011-06-01
Packaged: 2018-09-03 09:51:22
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,359
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8707741
Author URL: https://archiveofourown.org/users/sinfuldesire_archivist/pseuds/sinfuldesire_archivist
Summary: Sam is vanilla and Dean thinks it might be fun to show his brother something new. When Sam loses a bet Dean takes charge.





	

**Author's Note:**

> Note from the Sinful Desire archivists: this story was originally archived at [Sinful-Desire.org](http://fanlore.org/wiki/Sinful_Desire). To preserve the archive, we began importing its works to the AO3 as an Open Doors-approved project in November 2016. We e-mailed all creators about the move and posted announcements, but may not have reached everyone. If you are (or know) this creator, please contact us using the e-mail address on [Sinful Desire collection profile](http://archiveofourown.org/collections/sinfuldesire/profile).
> 
>  **Author's notes:** Beta'd by sbear51482 !

Dean knew that he was driving Sam insane. It was how he had planned it. What he had wanted. It might be mean and kind of evil, but what else could he do? He loved his brother, really, but this whole vanilla bean vibe that he had, it needed to go somewhere. Dean and sex was the natural order of things and he wasn't trying to make it with everyone that he crossed paths with, not since he and Sam started hooking up, but Sam wasn't as innocent as he thought he was. Dean knew his brother and he could deny it all he wanted, he could fear it all he wanted, but it didn't change anything. 

 

He had watched the lust grow in his brother's eyes for the last twelve or fourteen hours. They had been working a case which turned out to be nothing but a waste of their time. It didn't matter though, he’d got the plug going whenever Sam was sitting in the car with him, sitting at the library, right before whoever they were interviewing walked back into the room, it was kind of funny really. Dean'd shoved the plug into Sam that morning and had been jerking him around with it ever since. Well, not totally jerking him around because with the cock ring in place Sam was nice and hard, leaking but hopelessly unable to get off. 

 

The bet was simple, but the point was that Dean had won. Sam had whined and bitched but a bet was a bet and the point was that Sam would like this no matter how much he thought otherwise. Sex was supposed to feel good but a little pain here and there made it better, so did a little fear and humiliation. Dean pulled his jacket off once they got back into their motel room and he fully intended on making Sam get shit started here. He would still be Dean’s, at least until tomorrow morning. “So, Sammy, want to watch a movie?” he asked, smug and rather teasing.

 

Sam tightened his jaw, jutted out his chin moodily, and braced his hands on his hips. “This isn’t funny anymore, Dean. Take this shit off of me and be done with it.” Anger was the only way to keep from going insane, and the insanity rioting in his dick and balls, low in his belly, burning along his nerves, just inched the anger higher. It pissed him off because he’d made a deal and couldn’t end the torture himself, bound by his word and the threat of giving up sex for three months if he broke his promise.

 

Dean cleared his throat and shook his head. "Hey, you made the deal, stick with it. It isn't like blue-balls is going to kill you, is it?" he asked as he moved closer to his brother. "Besides, you’ve still got, what, ten hours to go before everything is said and done? And, honestly, I've just begun."

 

“I hate you,” Sam grumbled and sank gingerly down onto the end of the bed, squirming uncomfortably as the plug shifted inside him. It wasn’t so much that he didn’t like what Dean was doing to him—he didn’t, and that was the story he was sticking to—but Dean was so goddamn smug about it, cocky and grinning like he’d just won the lottery.

 

Dean moved in front of his brother and reached down to the hem of his shirt and pulled it up and over his head. He laughed gently. "Now, that sort of hurt my feelings, Sam. I mean, I should seriously punish you but I'm too nice and you aren't even remotely able to handle serious kink just yet," he answered as he pushed his brother back onto the bed.

 

A look of fearful horror crossed Sam’s face, quickly replaced with discomfort as the plug shifted inside him again. “You’re goddamn right I’m not ready for serious kink; I’m not ready for this much kink! I told you I don’t like this,” he muttered petulantly.

 

Dean looked as his brother as he joined him on the bed and sighed a little. He pushed Sam to lay on his stomach before reaching for the nightstand. He didn't say anything as he pulled the handcuffs out, pinned Sam's wrists above his head and snapped the cuffs around them and snapped them in place, locking them to the head board. After a few minutes, and after working Sam's jeans and boxers off, he finally spoke. "Don't lie to me, Sam, you can't and you know it," he said matter of fact. His brother had no choice but to listen tonight and Dean wasn't giving any middle ground. "You know I would never hurt you, so relax."

 

Sam groaned and planted his face in the blankets, still musky from where they’d fucked that morning. He sighed and turned his head to look at Dean over his shoulder. “Fine, okay; I’ll… I’ll try to enjoy it, but—stop looking so fucking smug.”

 

Smiling, he ran a hand down Sam's spine and nodded. "Good boy," he murmured as he grabbed the remote from his discarded jacket. Turning it on very low, Dean’s eyes moved back to his brother's form. "There are so many things I could do to you, Sam, but I'm going to be gentle. You have been so damn stubborn and you have to be honest with me." He turned off the plug off and sat back. "Now tell me the truth; have you really never wanted to do anything remotely close to this before, or never wanted to do it to me?"

 

A shiver raced down Sam’s spine as the plug abruptly stopped vibrating inside him and he drew in a deep, shaky breath to calm down again. “Tried some of it in college; wasn’t my kind of thing,” he said vaguely, dropping his head to the bed again.

 

"What did you try?" Dean asked, keeping up that line of questions since Sam seemed suddenly talkative about it for a change. "And what about it didn't you like?" he added. Sam loved sex, Dean knew that, he just didn't understand why trying something new was so out of the question.

 

“God, I really hate you,” Sam grumbled and rubbed his nose on his bicep, rubbing away an itch. “Frat house, Alpha Epsilon Pi, was taking pledges and part of the hazing was to survive a night at a BDSM club. I got spanked, nipple clamps, and paraded around naked with a collar on for about four hours before I told them to stick it in their ass and walked out.”

 

Dean was a little surprised at that one and, then again, if Sam had a bad time then no wonder he wasn't into it now. He hit the plug again though, a lot faster this time and sighed. "You know this ‘I hate you’ thing is really hitting a sore spot so you might want to keep from using it again," he growled as he turned it off again. "So, what, too much too fast?" he asked, going back to what Sam had just explained.

 

Another hard shudder went through Sam’s body at the sudden lack of vibration. It seemed that as soon as he got used to it and started trying to block it out, Dean shut the damn thing off again and left him feeling more sensitive to it. “Sorry. Just… sorry. I won’t say it again.” Sam sighed again and peeked over his shoulder at his brother. “More like a room full of extremely kinky people touching me and hitting me and offering to buy my ass for the night that turned me off to it.”

 

He knew what Sam was doing when he saw Sam tense and relax again. Dean shifted a little and looked back at Sam. "You like it when I touch you, though, and you know me. Bet that you wish I would touch you right now, huh?" 

 

“And that, right there, is why I’m so pissed at you; smug and knowing and pushing my buttons because you freaking can.” Sam pulled himself up the bed a bit, making some slack so that he could push up on his elbows, see Dean better. “Yeah, I like it when you touch me and, fuck, I want you to touch me, I just don’t see why you’ve got to use goddamn toys and shit on me.” Insecure? Surely not, but then he was a Winchester, and even if he did feel insecure, he fell right in line with the family motto: repress, repress, repress.

 

"No, Sam, you’re pissed at me because you like it and you don't want to admit it." Dean got up on his knees and put a hand in the middle of Sam's back. "How does it make you feel, Sam, to know that you can’t come unless I let you?" he asked as he moved down until he was breathing just by Sam's ear. "How would you like it if you had that type of power over me?" he expected answers too, to all the questions he had. If Sam wouldn’t give it up freely, then Dean would make him.

 

Sam shivered and closed his eyes, letting his head hang between his shoulders. Having any kind of power over Dean was something Sam had tried to get forever, thought he finally had it when Dean had given in and agreed to the new level in their relationship, but Dean was a freaking extremist and couldn’t just be happy with having access to Sam’s body and heart—no, Dean wanted full access, ownership rights, and, knowing Dean, bragging rights. 

 

Still, Sam knew an order when he heard it, and since Dean was the boss for the day, he had no choice but to answer truthfully. “Don’t like spending all damn day with a freaking hard on, don’t like that you fucking turned that damn thing on while we were on the job—what if it had ended up being an actual job and I was too fucking horny to think straight?” he growled, glad he’d taken the time to come up with a valid argument between going out of his freaking mind with pleasure. “As for having that kind of power over you, I’m not going to say it wouldn’t be nice, but I’m happy with you just as you are.”

 

Sam misunderstood Dean completely, he was happy with Sam, he was willing to give Sam everything, control included when he craved it. However, in order to give Sam anything and everything that he wished Dean had to know what it was that Sam desired. Dean knew what he liked but he hadn't had all that time to really get into it between taking care of Sam when he was younger, hunting and now…. Well, now he had Sam, he didn't want to learn anything new with anyone else. It wasn't a bad thing to want to share everything with the person that he loved and hiding part of himself as he had been wasn't fair to either of them.

 

Dean hovered over Sam and dropped his head to kiss his way down Sam's neck. He took a deep breath and let his hands run down Sam's sides and rubbed away the tension. "I knew that the job was a bust, don't ask me how, just trust me on this one," he answered. "You say that you love me for who I am, and I know that you do, but what you don't know is that you couldn't possible love all of me when you’re rejecting half of it. Not even bothering to look into the dark corners and see what you find before disregarding them."

 

Yeah, they’d both known that the job was a bust pretty much from the second day looking into it, but they’d had jobs like that before that had ended up being actual jobs instead of some moron playing practical jokes like their most recent one had been. Sam slumped forward onto the bed, elbows sliding out from beneath him. “I said I’d do what you wanted. I’m just telling you that, so far, this shit hasn’t been a picnic. I’ve been going out of my freaking mind all damn day and all you’ve done is laugh at me. Not exactly engendering fuzzy-happy feelings about this, dude.”

 

"Sam, stop fucking whining. You have your head so far up your ass about this; you're right this isn't going to go anywhere because you don't want to bother trying and you walking into this with this asshole outlook on it." Dean grabbed the plug and worked its way out of Sam's body. "Alright, fine Sam," he said, undoing the cuffs next. "You can’t find pleasure in it then I won't bother, ya happy now?" he asked as he threw the stuff off to the side. Dean had hoped that Sam would give in, find some enjoyment in it but he didn't seem to be able to give in or he didn't seem willing to at least try. Dean didn't want Sam to just do what he wanted, he wanted his brother to just give in once in a while and he didn't so they would stay boring and vanilla, maybe that would make Sam happy.

 

Sam rolled over and sat up beside his brother, staring at the wall across from the bed. “Are you done throwing your little temper tantrum now?” he asked, and without waiting for an answer, he continued. “Good, because if anyone’s got their head up their ass, it’s you. I said I’d do what you wanted, I wasn’t bitching about that. I’m bitching because I’ve had goddamn blue balls all day and you kept teasing me, kept pushing and pushing and when I’d start begging you to fucking do something about it, you laughed and said ‘later’, like it was supposed to make it all better.

 

“You want kinky, fine; let’s do kinky. But, goddamn it, don’t be a cock tease and then laugh about it when I’m all but on my knees begging you to make it stop.” Sam shot a brief glance over at his brother, lips tight. “It was fun until it started hurting, and not in a fun way.” He looked down at his dick, weeping and dark purple, and then back up at his brother. “Have you seen what this shit looks like? Have you ever been teased repeatedly for over ten hours and not allowed to come, not able to come?”

 

Obviously they were remembering things differently because if Sam had really given Dean what he wanted in all this it wouldn't have gone this far and it wouldn't have lasted this long. Dean knew what he was doing and there was no way in hell that Dean would torture Sam as badly as Sam wanted to put off that he had done. 

 

So Sam had gone from ‘please, please, please’ to laying there bitching about how Dean was laughing at him which Dean hadn't done. Maybe Sam's blue balls were escalating to such angst filled and dramatic terms. "What part of what I said, when I first brought this up, did you not understand, Sam?" he asked. "I don't want you to just do it because it will make me happy, I want you to be happy to but I guess I was wrong, this isn't doing anything for you so I'm done.

 

"And, yes, I have and I've had someone ignore my pleas; that's why I can honestly say what I would have never done that to you. If you would have done something other than make a bitch face at me, if you would have broken down and just told me what you wanted then it would have stopped, but you didn't and nothing you’re going to say is going to change the fact that this was a waste of time on both our parts and I'm done with it."

 

“Fine,” Sam huffed and grabbed his clothes from the floor, stood up and hobbled into the bathroom, slamming the door loudly behind him. Dean grabbed his jacket and headed for the door. He wasn't taking off but he needed air. He slammed the door and headed to his car, sitting on the hood. There were times Dean wished he fucking smoked.

 

Dean lay back on the hood of his car and just relaxed. Or, well, he tried to relax but it wasn't easy coming. Off all the people Dean had ever known or ran into over his years as a hunter, Sam outweighed all of them. That was because out of all of them, Sam was the one he actually gave a shit about but this time, he was just tired of giving in. He’d wait awhile and at some point he'd head back in, with any luck Sam would be asleep by then or at the very least in bed.

 

He had spent the better part of his life giving Sam everything he wanted, giving Sam everything that Dean could give him. Sam wanted to be stubborn then fine, but this time Dean wasn't giving in either. He was not going to head back into the motel to love on Sam, beg forgiveness and put it behind them like it didn't matter because, to Dean, it mattered. For Sam, Dean went against all rights, wrongs and instincts, it was how he was. He got up and got in the car, turning it on but leaving it in park to listen to music. 

 

Once the door slammed behind Dean, Sam dropped his clothes on the counter by the sink and carefully unfastened the cock ring, grimacing at the throbbing ache left behind, pounding in time with his angry heartbeat. He really wanted to get off, but jerking off alone had begun to feel hollow since he and Dean had added sex to their co-dependent relationship. Instead, Sam started up the shower and turned the taps to cold before stepping in. It was the most effective way to kill a hard on, even though it was the one that sucked the most.

 

Sam scrubbed off the sweat of the day, the sticky, tacky film of pre-come on his belly, and finished his shower as fast as he could. He figured Dean would be outside awhile, so he dressed quickly and went out to the table, dragging his laptop over and booting it up. He hated that he’d disappointed his brother, but Dean knew him well enough to know that Sam was more likely to get pissed off before he begged for anything. Even with sex. Most especially with sex; Sam could be a patient lover, but teasing for hours of end tended to make him irritable rather than make him buckle and beg. He just wasn’t wired that way; John hadn’t raised them to buckle under pressure. He’d raised them to get mad and use that anger to get through the situation. 

 

The laptop logged in and Sam started searching for another hunt, eager to get another job in his sights so that he could work off the irritation and anger—God knew he wouldn’t be able to turn to Dean for relief, not now, probably not ever again. Sam sighed and scrubbed a hand over his face, feeling hollow as the realization settled in.

 

Two hours in and Sam still had nothing, which wasn’t exactly surprising since the bust case had been the only thing popping up lately. Sam scrubbed a hand over his face and shut his laptop down, giving up the search for the night, and stripped out of his jeans. He left his tee shirt and boxers on and crawled into the far bed, glad, for once, that they still got two queens, and huddled near the far edge, as far from Dean’s bed as he could get. 

 

He was exhausted after being ridden hard with lust and need all day, but Sam couldn’t go to sleep until Dean came back, until the familiar sounds of Dean moving about the room lulled him into a sense of security. He might’ve fucked everything up between them, but he wasn’t afraid that Dean would abandon him because of it. It would just take some… some getting used to again, that inability to touch or be close. Sam’s chest tightened but there wasn’t anything he could do about it. Even when he’d tried to tell Dean that he was okay with it, to just do something, it had blown up in his face. Message received: game over.

 

Dean stayed in the car and made it through the Black Album at least three times before getting out and stretching, ready to sleep. Making his way into the room again, he looked at the bed he thought they had shared the night before and then the one Sam was in. He settled on sleeping with Sam; he was tired and confused and slipped into the same bed as his brother before turning on his side, assuming Sam was asleep, and settled in to try and join him.

 

It was a bit of a surprise that Dean had crawled in with him; Sam had expected to hear the springs of the other bed creak and cement the idea that he’d screwed up completely. It just—that wasn’t what happened. He could feel the heat of Dean’s body behind him, smell the subtle scent of Dean’s aftershave, worn away after a day spent out talking to witnesses and dealing with diner waitresses and librarians.

 

Comfort settled the sharp pang of loss, changed it and rearranged it into relief; Dean hadn’t cut him off, hadn’t stamped void on their sex life. Sam rolled over and spooned up against Dean’s back, an arm slung over his brother’s waist. “I wanted to try it because it’s something you’re into, wanted to, Dean. Still want to, if you do, and I’ll try to give in instead of getting bitchy,” he whispered against the back of Dean’s neck.

 

Dean closed his eyes, took a deep breath, and opened them again. After a few hours out in the cold he finally let his body relax. He pushed back into Sam, soaking up in the warmth. He made a face, didn't say anything for a second, because he wasn't sure what he could say. Sam seemed so dead set against it and Dean didn't want to hurt Sam and he didn't want to fuck them up. Their relationship was screwy to say the least, even if it did work for them most of the time. "Sam, I won't push you into something you don't like. I'm always up for trying new things but not at the cost of one or both of us being uncomfortable or unhappy about it. I just want you to enjoy yourself, but you can't force yourself and it’s unfair for me to try and make you."

 

“Dean,” Sam murmured, lips dragging faintly against the back of Dean’s neck as he spoke, “I don’t think you understand me. I want to do this, wanna try it with you, see if I could like it. I, I did what dad taught us to do: don’t lose my head, just get angry. I do want to try this, but I draw the line at nipple clamps—those bastards hurt, and if you try to give me an enema, I will shove the Impala up your ass. Don’t hurt me and don’t try to lead me around out in public on a dog leash and we’re good.”

 

If anyone should understand that logic it was Dean. Anger was a weapon and the brothers always used it. Dean turned a bit to face his brother. "We'll talk about everything before we try?" he asked warily. "I would never hurt you, Sam. And, yeah, I don't do water sports and puppy play so we should be okay, I guess." A smirk curved one corner of his lips. "Besides, if you do like it, who knows, you might actually have something you want to try," he teased though he wasn't all that sure this was still Sam they were talking about.

 

Sam chuckled and scraped his teeth over the nape of Dean’s neck lightly. “I’m sure that if there’s a kink out there, you’ve already done it or thought of it. Still, I’ll take it into consideration if this turns out to be as fun as you make it seem.”

 

Logs:

 

Dean smirked and rolled his eyes. "Yeah, but this is the first time I've ever done any of this stuff with my brother so it'll be so much dirtier," he joked as he kissed Sam's temple.

 

“Dude, all we have to do is have sex and we’re getting kinky; what could possibly be kinkier than fucking your brother?” Sam asked and then immediately slapped a hand over Dean’s mouth. “And don’t even bring dad into this.”

 

Dean grinned; Sam always knew how his mind worked. He pulled Sam's hand away and turned on his side to look at his brother. "You just spent all day with a plug shoved up your ass; do you really want to ask me how kinky I can be?" 

 

“A plug isn’t too kinky. I mean, it’s not like fucking outside or making you dress in drag and suck my cock.” Sam grinned, getting into the idea of how this kink thing could go both ways.

 

Laughing Dean rolled his eyes. "Oh man, I'm going regret this; I see it already." He shook his head. "See, I knew you could get into this, but just keep in mind that whatever you do to me I'm going to hit you twice as hard."

 

“No, Dean, you’re not going to regret it. You’re gonna love every second of it.” Sam leaned in and caught his brother’s mouth in a laughing kiss, rolling him beneath him. “And maybe I’ll like it too.”

 

Dean’s arms came up around Sam and pulled him down to lay on top of him. "I'll make sure you do, baby, I promise." 

 

~*~END~*~


End file.
